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WO2020061223A1 - Nouvelles petites molécules qui améliorent les qualités de sapidité du café et de boissons associées - Google Patents

Nouvelles petites molécules qui améliorent les qualités de sapidité du café et de boissons associées Download PDF

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Publication number
WO2020061223A1
WO2020061223A1 PCT/US2019/051780 US2019051780W WO2020061223A1 WO 2020061223 A1 WO2020061223 A1 WO 2020061223A1 US 2019051780 W US2019051780 W US 2019051780W WO 2020061223 A1 WO2020061223 A1 WO 2020061223A1
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WIPO (PCT)
Prior art keywords
coffee
group
compounds
acid group
caffeic acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2019/051780
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English (en)
Inventor
Devin PETERSON
Sichaya SITTIPOD
Eric Schwartz
Laurianne PARAVISINI
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Ohio State Innovation Foundation
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Ohio State Innovation Foundation
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Publication date
Application filed by Ohio State Innovation Foundation filed Critical Ohio State Innovation Foundation
Priority to EP19863400.8A priority Critical patent/EP3852542A4/fr
Priority to US17/277,465 priority patent/US11856975B2/en
Publication of WO2020061223A1 publication Critical patent/WO2020061223A1/fr
Anticipated expiration legal-status Critical
Priority to US18/512,661 priority patent/US12213502B2/en
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/88—Taste or flavour enhancing agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F5/00—Coffee; Coffee substitutes; Preparations thereof
    • A23F5/02—Treating green coffee; Preparations produced thereby
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F5/00—Coffee; Coffee substitutes; Preparations thereof
    • A23F5/46—Coffee flavour; Coffee oil; Flavouring of coffee or coffee extract
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F5/00—Coffee; Coffee substitutes; Preparations thereof
    • A23F5/46—Coffee flavour; Coffee oil; Flavouring of coffee or coffee extract
    • A23F5/48—Isolation or recuperation of coffee flavour or coffee oil
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F5/00—Coffee; Coffee substitutes; Preparations thereof
    • A23F5/46—Coffee flavour; Coffee oil; Flavouring of coffee or coffee extract
    • A23F5/48—Isolation or recuperation of coffee flavour or coffee oil
    • A23F5/50—Isolation or recuperation of coffee flavour or coffee oil from coffee extract
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/28—Coffee or cocoa flavours

Definitions

  • the invention is the isolation of flavor enhancing components of coffee, and the use of these compounds to improve the overall quality of a coffee and related beverages.
  • the chemical composition of coffee brew is known to consist of a complex mixture of thousands of compounds endogenous to the green coffee beans or generated during post-harvest fermentation or roasting steps (Clifford, 1985). Thermal generation of flavor during roasting is known to be highly dependent on the green bean composition and the degree of roasting which impact the flavor of the final brew (Buffo & Cardelli-Freire, 2004). Several factors from farm to cup are known to influence coffee flavor quality such as species/cultivars, geographical origin, green bean processing method, roasting and storage (Feria-Morales, 2002; Sunarharum,
  • Figure 1 depicts an experimental approach to identify flavor enhancing compounds in coffee.
  • Figure 2 depicts a process for selecting markers responsible for improving coffee quality.
  • Figure 3 depicts a schematic for the isolation of flavor enhancing compounds.
  • Figure 4 depicts quantitative profiles for certain flavor enhancing compounds.
  • Figure 5 depicts the combination of initial coffee quality with a flavor enhancing compound to increase overall coffee quality.
  • Figure 6 depicts the sensory impact of positive markers on sensed coffee quality.
  • Figure 7 depicts the specific flavor improvements in coffee, while also showing that the flavor enhancing compound, apart from coffee, does not produce any olfactory sensation
  • Figure 8 depicts the retention time and m/z for certain flavor enhancing and flavor diminishing compounds.
  • Figure 9 depicts quantitative profiles of compounds correlating with increasing cup score, and compounds correlating with decreasing cup score.
  • Figures 10 and 11 depict the specific flavor enhancing effect of certain compounds.
  • Figures 12 and 13 depict the general flavor reduction achieved with certain compounds.
  • Figures 14 and 15 depict the specific flavor reducing effect of certain compounds.
  • Figures 16 and 17 depict the occurrence of certain compounds in green and roasted beans.
  • Figure 18 depicts relative concentration of 3-0-caffeoyl-4-0-3-methylbutanoylquinic acid (CMBQ) in green and roasted coffee beans to internal standard; eclipse highlight samples had noted flavor defects.
  • CMBQ 3-0-caffeoyl-4-0-3-methylbutanoylquinic acid
  • the word“comprise” and variations of the word, such as“comprising” and“comprises,” means“including but not limited to,” and is not intended to exclude, for example, other additives, components, integers or steps.
  • “Exemplary” means“an example of’ and is not intended to convey an indication of a preferred or ideal embodiment. “Such as” is not used in a restrictive sense, but for explanatory purposes. Disclosed are components that can be used to perform the disclosed methods and systems. These and other components are disclosed herein, and it is understood that when combinations, subsets, interactions, groups, etc.
  • alkyl as used herein is a branched or unbranched hydrocarbon group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, and the like.
  • the alkyl group can also be substituted or unsubstituted. Unless stated otherwise, the term“alkyl” contemplates both substituted and unsubstituted alkyl groups.
  • the alkyl group can be substituted with one or more groups including, but not limited to, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, nitro, silyl, sulfo-oxo, or thiol.
  • An alkyl group which contains no double or triple carbon-carbon bonds is designated a saturated alkyl group, whereas an alkyl group having one or more such bonds is designated an unsaturated alkyl group.
  • Unsaturated alkyl groups having a double bond can be designated alkenyl groups, and unsaturated alkyl groups having a triple bond can be designated alkynyl groups. Unless specified to the contrary, the term alkyl embraces both saturated and unsaturated groups.
  • cycloalkyl as used herein is a non-aromatic carbon-based ring composed of at least three carbon atoms.
  • examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • heterocycloalkyl is a cycloalkyl group as defined above where at least one of the carbon atoms of the ring is replaced with a heteroatom such as, but not limited to, nitrogen, oxygen, sulfur, selenium or phosphorus.
  • the cycloalkyl group and heterocycloalkyl group can be substituted or unsubstituted.
  • the terms“cycloalkyl” and“heterocycloalkyl” contemplate both substituted and unsubstituted cyloalkyl and heterocycloalkyl groups.
  • heterocycloalkyl group can be substituted with one or more groups including, but not limited to, alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, nitro, silyl, sulfo-oxo, or thiol.
  • a cycloalkyl group which contains no double or triple carbon-carbon bonds is designated a saturated cycloalkyl group, whereas an cycloalkyl group having one or more such bonds (yet is still not aromatic) is designated an unsaturated cycloalkyl group.
  • the term cycloalkyl embraces both saturated and unsaturated, non-aromatic, ring systems.
  • aryl as used herein is an aromatic ring composed of carbon atoms.
  • aryl groups include, but are not limited to, phenyl and naphthyl, etc.
  • heteroaryl is an aryl group as defined above where at least one of the carbon atoms of the ring is replaced with a heteroatom such as, but not limited to, nitrogen, oxygen, sulfur, selenium or phosphorus.
  • the aryl group and heteroaryl group can be substituted or unsubstituted. Unless stated otherwise, the terms“aryl” and“heteroaryl” contemplate both substituted and unsubstituted aryl and heteroaryl groups.
  • the aryl group and heteroaryl group can be substituted with one or more groups including, but not limited to, alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl,
  • heterocycloalkyl aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, nitro, silyl, sulfo-oxo, or thiol.
  • heteroaryl and heterocyclyl rings include: benzimidazolyl, benzofuranyl, benzothiofuranyl, benzothiophenyl, benzoxazolyl, benzoxazolinyl, benzthiazolyl, benztriazolyl, benztetrazolyl, benzisoxazolyl, benzisothiazolyl, benzimidazolinyl, carbazolyl, 4aH carbazolyl, carbolinyl, chromanyl, chromenyL cirmolinyl, decahydroquinolinyl, 2H,6H ⁇ l,5,2-dithiazinyl, dihydrofuro[2,3 bjtetrahydrofuran, furanyl, furazanyl, imidazolidinyl, imidazolinyl, imidazolyl, lH-indazolyl, indolenyl, indolinyl, indolizinyl
  • alkoxy “alkoxy,”“cycloalkoxy,”“heterocycloalkoxy,”“cycloalkoxy,”“aryloxy,” and “heteroaryloxy” have the aforementioned meanings for alkyl, cycloalkyl, heterocycloalkyl, aryl and heteroaryl, further providing said group is connected via an oxygen atom.
  • the term“substituted” is contemplated to include all permissible substituents of organic compounds.
  • the permissible substituents include acyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, and aromatic and nonaromatic substituents of organic compounds.
  • Illustrative substituents include, for example, those described below.
  • the permissible substituents can be one or more and the same or different for appropriate organic compounds.
  • the heteroatoms such as nitrogen, can have hydrogen substituents and/or any permissible substituents of organic compounds described herein which satisfy the valencies of the heteroatoms.
  • This disclosure is not intended to be limited in any manner by the permissible substituents of organic compounds.
  • the terms“substitution” or“substituted with” include the implicit proviso that such substitution is in accordance with permitted valence of the substituted atom and the substituent, and that the substitution results in a stable compound, e.g ., a compound that does not spontaneously undergo transformation such as by rearrangement, cyclization, elimination, etc.
  • a substituent that is said to be“substituted” is meant that the substituent can be substituted with one or more of the following: alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halide, hydroxy, ketone, nitro, silyl, sulfo-oxo, or thiol.
  • groups that are said to be substituted are substituted with a protic group, which is a group that can be protonated or deprotonated, depending on the pH.
  • Acceptable salts are salts that retain the desired flavor enhancing activity of the parent compound and do not impart undesirable toxicological effects.
  • examples of such salts are acid addition salts formed with inorganic acids, for example, hydrochloric, hydrobromic, sulfuric, phosphoric, and nitric acids and the like; salts formed with organic acids such as acetic, oxalic, tartaric, succinic, maleic, fumaric, gluconic, citric, malic, methanesulfonic, p-toluenesulfonic, napthalenesulfonic, and polygalacturonic acids, and the like; salts formed from elemental anions such as chloride, bromide, and iodide; salts formed from metal hydroxides, for example, sodium hydroxide, potassium hydroxide, calcium hydroxide, lithium hydroxide, and magnesium hydroxide; salts formed from metal carbonates, for example, sodium carbonate, potassium carbonate, calcium carbonate, and magnesium carbonate; salts
  • Pharmaceutically acceptable and non- pharmaceutically acceptable salts may be prepared using procedures well known in the art, for example, by reacting a sufficiently basic compound such as an amine with a suitable acid comprising a physiologically acceptable anion.
  • a sufficiently basic compound such as an amine
  • a suitable acid comprising a physiologically acceptable anion.
  • Alkali metal for example, sodium, potassium, or lithium
  • alkaline earth metal for example, calcium
  • a formula with chemical bonds shown only as solid lines and not as wedges or dashed lines contemplates each possible isomer, e.g., each enantiomer and diastereomer, and a mixture of isomers, such as a racemic or scalemic mixture.
  • Compounds described herein can contain one or more asymmetric centers and, thus, potentially give rise to diastereomers and optical isomers.
  • the present invention includes all such possible diastereomers as well as their racemic mixtures, their substantially pure resolved enantiomers, and all possible geometric isomers.
  • the perceived quality of a cup of coffee is impacted both by the specific flavors in the coffee, as well as the aroma of the coffee. Differences in aroma are perceived by the olfactory system. Differences in flavor are perceived in the gustation system, in which compounds interact with taste bud pores in the alimentary system. Differences in flavor are perceived by the somatosensory system, which can occur anywhere in the body, relating to or denoting sensations such as pressure, pain, or temperature. Chemesthesis is the direct activation of somatosensory nerves by chemical stimuli. The combination of these senses contribute to the overall perceived quality of the coffee.
  • the quality of a particular cup of coffee can be assessed using the Cup Score system, established by the Specialty Coffee Association (“SC A”), and determined by one or more certified industrial Q graders.
  • the maximum cup score is 100.
  • Coffee can be broken in to two general categories based on cup score of‘sub-specialty’ (less then 80) and‘specialty coffee’ (equal to or greater than 80); within the specialty coffee, further categories are designated with increasing cup score, such as very good specialty (80-84.99), excellent specialty (85-89.99), and outstanding specialty (90-100) according to SCA cupping method; generally commercial samples in North America range in cup score between 75-90.
  • Three quality groups based on cup score were assigned: high quality coffee has a cup score greater than 85, medium quality coffee has a cup score between 80-84.99, and low quality coffee has a cup score less than 80.
  • the compounds disclosed herein may be added to an already brewed cup of coffee to enhance its quality. For instance, a low quality coffee may be converted to a medium or high quality coffee, a medium quality coffee may be converted to a high quality coffee, and a high quality coffee may be further enhanced to have an even high cup score.
  • the compounds disclosed herein may be added in order to enhance the cup score by at least 5%, at least 10%, at least 15%, and least 20%, or at least 25%, relative to the cup score of the starting coffee.
  • the compounds disclosed herein may be added to give a final coffee having a cup score from 80-100, from 85-100, from 87.5-100, from 90-100, from 92.5-100, from 95-100, or from 97.5-100.
  • the compounds disclosed herein may be added to coffee beans, fermented coffee bean, roasted coffee beans, or ground coffee beans in order to enhance the quality of a coffee cup obtained from said beans.
  • a low quality coffee bean may be converted to a medium or high quality coffee bean
  • a medium quality coffee bean may be converted to a high quality coffee bean
  • a high quality coffee bean may be further enhanced to provide an even high cup score.
  • the compounds disclosed herein may be added to the beans in order to enhance the cup score of a coffee cup obtained therefrom by at least 5%, at least 10%, at least 15%, and least 20%, or at least 25%, relative to the cup score of the coffee.
  • the compounds disclosed herein may be added to give a final coffee having a cup score from 80-100, from 85-100, from 87.5-100, from 90-100, from 92.5-100, from 95-100, or from 97.5-100.
  • the flavor enhancing compounds may be added to coffee beans or grounds to increase the concentration of the compounds relative to unadulterated coffee beans or grounds.
  • the disclosed compounds may be added, for instance in an amount of at least 5 mg/kg, at least 10 mg/kg, at least 20 mg/kg, at least 30 mg/kg, at least 40 mg/kg, at least 50 mg/kg, at least 60 mg/kg, at least 70 mg/kg, at least 80 mg/kg, at least 90 mg/kg, at least 100 mg/kg, at least 200 mg/kg, at least 300 mg/kg, at least 400 mg/kg, or at least 500 mg/kg relative to the total weight of the coffee beans or grounds.
  • the disclosed compounds can be added to soluble (i.e., instant) coffee compositions in similar amounts.
  • the disclosed compounds may be added in an amount from 5-50 mg/kg, from 50- 100 mg/kg, from 100-200 mg/kg, from 100-500 mg/kg, from 100-1,000 mg/kg, from 250-500 mg/kg, from 250-750 mg/kg, from 250-1,000 mg/kg, or from 500-1,000 mg/kg.
  • the compounds may be added to coffee beans, grinds and/or soluble (i.e., instant) coffee compositions in a variety of different manners.
  • the compounds may be directly admixed with dry beans, grinds and/or soluble coffee compositions in the
  • the compounds may be dissolved or dispersed in a solvent, either water or organic solvent, and then combined with the beans or grinds for a time sufficient to impart the desired concentration of compounds in the beans or grinds.
  • the compounds may be combined with coffee during various stages of its processing.
  • the compounds may be added prior to roasting, during roasting, after roasting, prior to fermentation, during fermentation, after fermentation, prior to grinding, during grinding, after grinding, prior to brewing, during brewing, after brewing, or after brewing and drying.
  • Coffee beans e.g., green coffee beans
  • the compounds can be directly added to the fermentation broth.
  • the disclosed compounds may be added to an already brewed beverage such that the final concentration of the compound is from 0.01-100 mg/L, from 0.1-100 mg/L, from 0.5-50 mg/L, from 0.5/25 mg/L, from 0.5-15 mg/L, from 1-15 mg/L, from 5-15 mg/L, or from 5-10 mg/L.
  • the compounds disclosed herein may be used as molecular targets for breeding programs to obtain coffee beans enriched with the compounds.
  • the breeding programs can encompass natural processes such as cross-breeding and selective environmental pressure, as well as recombinant techniques.
  • the compounds disclosed herein may be used as markers for coffee producers to improve their processes for harvesting, roasting, and processing in order to increase the concentration of the compounds in the coffee.
  • the compounds may further be used to screen and develop fermentation cultures for enhancing production of the compounds.
  • the compounds can be a caffeic ester having the formula:
  • R is Ci-salkyl, C2-salkenyl, C2-salkynyl, aryl, Ci-sheteroaryl, C3-8cycloalkyl, or Ci- 8heterocyclyl.
  • R can be a C3-8cycloalkyl or aryl group having the formula:
  • R 1 , R 2 , R 3 , R 4 , R 5 , or R 6 represents a bond to the cinnamoyl group
  • R can be a cyclitol group.
  • a cyclitol group is a cycloalkyl group, preferably a C6 cycloalkyl group having at least two hydroxyl groups.
  • R can be a bomesitol group connected to the cinnamoyl group at the 1, 2, 3, 4, or 5 hydroxyl position;
  • R can be a conduritol group connected to the cinnamoyl group at the 1, 2, 3, or 4 hydroxyl position;
  • R can be a inositol group connected to the cinnamoyl group at the 1, 2, 3, 4, 5, or 6 hydroxyl position;
  • R can be a pinitol group connected to the cinnamoyl group at the 1, 2, 3, 4, or 5 hydroxyl position;
  • R can be a pinpollitol group connected to the cinnamoyl group at the 1, 2, 4, or 5 hydroxyl position;
  • R can be a quebrachitol group connected to the cinnamoyl group at the 1, 2, 3, 4, or 5 hydroxyl position;
  • R can be a quinic acid group connected to the cinnamoyl group at the 1, 3, 4, or 5 hydroxyl position;
  • the flavor enhancing compounds can have the structure:
  • R 1 , R 2 , R 3 , or R 4 is a caffeic acid derivative having the formula:
  • R a , R b , R c , R d , and R e are independently selected from F, Cl, Br, I, nitro, R, OR, N(R)2, SO2R, S0 2 N(R) 2 , C(0)R; C(0)0R, 0C(0)R; C(0)N(R) 2 , N(R)C(0)R, 0C(0)N(R lb’ ) 2 ,
  • R is in each case independently selected from hydrogen, Ci-salkyl, C 2 - salkenyl, C 2 -8alkynyl, aryl, Ci-sheteroaryl, C3-8cycloalkyl, or Ci-sheterocyclyl;
  • R 1 , R 2 , R 3 , and R 4 are independently selected from hydrogen, C(0)R; C(0)0R, and C(0)N(R) 2 , wherein R is in each case independently selected from hydrogen, Ci- 8alkyl, C 2 -8alkenyl, C 2 -8alkynyl, aryl, Ci-sheteroaryl, C3-8cycloalkyl, or Ci-sheterocyclyl;
  • R 5 is selected from OR or NR2, wherein R is independently selected from hydrogen, Ci- salkyl, C2-salkenyl, C2-salkynyl, aryl, Ci-sheteroaryl, C3-8cycloalkyl, or Ci-sheterocyclyl;
  • R 5 may form a bond with any of R 1 , R 2 , R 3 , or R 4 .
  • R 5 is a group having the formula -0-Ci-6alkyl.
  • Exemplary Ci-6alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and t-butyl.
  • each of the R 1 , R 2 , R 3 , or R 4 that is not the caffeic acid derivative will be hydrogen.
  • R 4 can be the caffeic acid derivative and each of R 1 , R 2 , R 3 , and R 5 are hydrogen.
  • R 3 can be the caffeic acid derivative and each of R 1 , R 2 , R 4 , and R 5 are hydrogen.
  • R 2 can be the caffeic acid derivative and each of R 1 , R 3 , R 4 , and R 5 are hydrogen.
  • R 4 is C(0)R, wherein R is Ci-6alkyl.
  • Ci-6alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and t-butyl, and isobutyl is often preferred.
  • R 3 is C(0)R, wherein R is Ci-6alkyl.
  • exemplary Ci-6alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and t-butyl, and isobutyl is often preferred.
  • R 3 can be C(0)R as defined above, R 4 is hydrogen, and R 2 is a caffeic acid derivative.
  • the caffeic acid derivative is the compound wherein R b and R c are each hydroxyl, and R a , R d , and R e are each hydrogen.
  • R 4 and R 5 will together form a bond, yielding a lactone compound having the formula:
  • R 1 , R 2 , and R 3 have the meanings given above.
  • R 5 and R 4 can form a bond
  • R 5 and R 3 can form a bond
  • R 5 and R 1 can form a bond
  • the flavor enhancing compounds will have the formula:
  • R 1 , R 2 , R 3 , R 4 , and R 5 are as defined above.
  • the above compound may be present as a racemic mixture or an enantioenriched compounds, for instance, having an enantiomeric excess ee of at least 75%, 80%, 85%, 90%, 95%, 97.5%, 99%, or 99.5%.
  • R 3 is C(0)R, wherein R is Ci- 6 alkyl.
  • Exemplary Ci- 6 alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and t-butyl, and isobutyl is often preferred.
  • R 3 can be C(0)R as defined above, R 4 is hydrogen, and R 2 is a caffeic acid derivative.
  • the caffeic acid derivative is the compound wherein R b and R c are each hydroxyl, and R a , R d , and R e are each hydrogen.
  • the flavor enhancing compounds will include reduced amounts of, or not include any, ent-kaurane type diterpenoids.
  • Such compounds are known to the those with skill in the art, and typically include a rearranged D-ring structure relative to normal steroid skeletons:
  • any carbon atom may be substituted with one or more oxygen or alkyl groups, and wherein a single bond may be replaced with a double bond, as permitted by valence.
  • Green coffee beans form the crop year 2015 to 2016 were sourced from importing companies in the United States from multiple origins around the world that included Ethiopia, Brazil, Colombia, Costa Rica, Kenya, Guatemala, Honduras, Sumatra, Philippine, Kenya, and Vietnam.
  • Green coffee beans were roasted to the SCA standard for optimal roasting conditions (SCA 2009). Freshly roasted beans were then allowed to degas for two days and then stored in glass bottles closed with PTFE lids after nitrogen flushing at -80°C. Coffee brew (5% ground/ water) was prepared from freshly ground coffee beans using a drip-coffee maker (Moccamaster KBT741, Technivorm, Italy). Two biological replicates were prepared for each coffee sample. Sample clean-up was performed on Oasis HLB prime 96-well plate cartridge, 10 mg bed (Waters, Milford, MA, USA).
  • Untargeted chemical profiling was performed using Ultra High-Performance Liquid Chromatography coupled with a Mass Spectrometer-Ion Mobility-Time of Flight UPLCMS-IM- QToF (Acquity H-Class quaternary flow solvent manager with Synapt G2-S, Waters, MA,
  • Electrospray ionization was run in negative mode with source temperature of 120 °C, desolvation temperature of 400 °C, capillary voltage was set to 2.5 kV, cone sample 40 V, Tof scan range was 50-1200 m/z and scan time was 0.3 sec for continuum data.
  • Internal reference compound Leucine-enkephalin (m/z 556.2771) was infused by a lock spray during data acquisition for mass correction. Each SPE replicate was injected 2 times in randomized order. Injection volume was 5 m ⁇ , with a column standard injected every l0 th run to check retention time shifts and mass spectrometer performance throughout experiment sequence.
  • the selected chemical features 4.13 _ 193, 7.00_437, 8.25_67l and 8.52_4l9 were isolated from coffee brew.
  • a total volume of 800 ml of coffee brew was loaded on to four Oasis HLB prime (Waters) 6 g bed cartridges.
  • An initial washing step was performed using 200 ml of 5% methanol/water.
  • Elution was performed in 4 steps using 50 mL of different ratios of methanol/water (40, 60, and 90%) and collected separately.
  • SPE fraction 60% contained features 4.13 193 and 7.00_437 and fraction 90% contained features 8.25_67l and 8.52_4l9.
  • the fractions were freed from solvent (Rocket Synergy Purge, Genevac, UK) and lyophilized.
  • SPE fraction 60% and fraction 90% methanol isolate were reconstituted in 30%, and 50%
  • LC/MS-QTof accurate mass analysis were carried out using a G6545B LC -QTof (Agilent Technologies, Santa Clara, CA).
  • a reverse phase Eclipse Plus C18 (2.1 x 50 mm, 1.8 pm, Agilent) was kept at 40°C in a 671767B Multisampler (Agilent).
  • Electrospray ionization was run in negative mode with desolvation gas at 350 °C and sheath gas at 375 °C.
  • Capillary voltage was 4.5 kV and nozzle voltage was 500 V.
  • Collision energy of 30, 30, and 40V was used for compound features 7.00_437, 8.52_4l9 and 8.25_67l (RT _m/z), respectively.
  • Isolated standards of features 4.13 _ 193, 7.00_437, 8.25_67l and 8.52_4l9 (KY_m/z) were used to quantify each compound in the brew of the three coffees ranged in cup score of different representative coffee classes (below specialty, very good specialty, and excellent specialty).
  • Quantification was carried out using 5-point external calibration curves for each compound in water and adjusted for the compound extraction recovery from coffee as determined by standard addition (in triplicate). Analyses were carried out using an Acquity Id- Class UPLC system coupled to a Xevo- TQ-S Mass Spectrometer (Waters). A reverse phase BEH C18 (2.1 x 50 mm, 1.6 pm, Waters) was kept at 40°C in a Waters column manager. A flow rate of 0.5 mL/min with a binary gradient mobile phase consisting of solvent (A) nanopure water with 0.1 % formic acid and (B) acetonitrile with 0.1% formic acid.
  • Electrospray ionization was run in negative mode with a source temperature of 120 °C, desolvation temperature of 550 °C, capillary 2.3 kV, and sample cone 20 V. Optimized MRM condition of each compound are presented in Table 1.
  • Methylparaben (internal standard) was monitored in ESI negative mode using the transition 153 -> 93 m/z.
  • the cup score was determined in coded samples using the official SCA cupping protocol (SC A, 2015), with five licensed Q-graders.
  • recombination models were prepared with each individual compound and a combination of all 4 compounds (totaling in 5 recombination models) which were evaluated with two control samples. All samples were blind coded, presented in a randomized order and evaluated using the cupping protocol by five certified Q-graders.
  • the purified compounds were also evaluated individually in water base at concentrations presented in Table 1 for, excellent specialty coffee, in both a buffer (0.025 M phosphate buffer adjusted to pH 5 with 0.1 M citric acid) and unbuffered (nanopure water) system.
  • a consensus panel of four experienced sensory evaluators was used to assess the flavor attributes of the compounds.
  • Unsupervised principle component analysis was modeled with the 2450 features to determine samples outliers and confirmed good reproducibility of data.
  • a supervised orthogonal partial least square (OPLS) model was then used to define predictive coffee compounds that corresponded to the SCA sensory coffee cup score (Figure la).
  • VIP values and/or VIP rank have been successfully used for feature selection of flavor relevant information (Iwasa et al., 2015; Ronningen et al., 2018)
  • a VIP value above 1 of a feature is typically used to indicate a significant contribution to the model (Galindo-Prieto, Eriksson, & Trygg, 2014).
  • the use of correlation and magnitude/fold change is also a common practice for feature selection
  • the 3 ⁇ 4 NMR spectrum further exhibited signals characteristic of a quinic acid group with three downfield signals at 5H 5.70, 5H 5.02, and 5H 4.24 corresponding to methine protons attached to oxygenated carbons.
  • Lactones of chlorogenic acid have been previously identified in roasted coffee (Schrader, Kiehne, Engelhardt, & Maier, 1996). Lactones are formed exclusively on chlorogenic acids free of substitution on C5 position and its formation is favored for 3-CQA over 4-CQA due to steric hindrance of the ester bond and the equatorial confirmation being more
  • somatosensory attributes For example, the recombination models were described with citrus, caramel and lemon fruit notes whereas the control was woody, old and astringent. Flavor attributes such as woody, old, and astringent which are typically associated with undesirable prolong storage of coffee (Bucheli, Meyer, Pittet, Vuataz, & Viani, 1998).
  • cellotretraose a tasteless cellooligosaccharride
  • was found to suppress bitterness of caffeine (Ley, 2008).
  • two of the three compounds identified were chlorogenic acid derivatives with a 3-methylbutanoic ester moiety.
  • chlorogenic acid compounds modified taste attributes such as sweetness enhancement (Upadhyay and Rao 2013) and bitter inhibition (Riemer, 1993).
  • the addition of 30 ppm of chlorogenic acid from an extract prepared from green coffee beans was found to reduce the metallic and bitter off-taste of an acidic beverage (Chi eng et al., 2002).
  • Chlorogenic acid’s ability to increase water solubility of certain volatiles has also been demonstrated (King and Solms 1982).
  • compound 3-methylbutanoic acid has been identified as a potent odorant in roasted coffee, exhibiting odor qualities such as sweaty and fermented (Blank, Sen, & Grosch, 1991; Blank, Sen, & Grosch, 1992; Holscher, Vitzthum, & Steinhart, 1990) and was suggested to contribute to the sour flavor of heated canned coffee drinks (Kumazawa & Masuda, 2003).
  • odor qualities such as sweaty and fermented
  • Approximately a 3-fold higher odor activity of 3-methylbutanoic acid was reported in Arabica coffee compared to Robusta coffee (Blank et al., 1991).
  • the prevalence of 3-methylbutanoic acid in disease-free green beans has been reported (Toci & Farah, 2008).
  • 3-0-caffeoyl-4-0-3-methylbutanoylquinic acid could be a plant metabolite.
  • VIP Variable influence on projection
  • OPLS orthogonal projections to latent structures
  • New bitter-masking compounds Hydroxylated benzoic acid amides of aromatic amines as structural analogues of homoeriodictyol. Journal of Agricultural and Food Chemistry , 54(22), 8574-8579.
  • composition and potent odorants of the“specialty coffee” brew“Bourbon Pointu” correlated to its three trade classifications. Food Research International, 61, 264-271.
  • compositions and methods of the appended claims are not limited in scope by the specific compositions and methods described herein, which are intended as illustrations of a few aspects of the claims and any compositions and methods that are functionally equivalent are intended to fall within the scope of the claims.
  • Various modifications of the compositions and methods in addition to those shown and described herein are intended to fall within the scope of the appended claims.

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Abstract

La présente invention concerne des composés à petites molécules qui peuvent être utilisés pour augmenter la qualité générale d'une boisson au café. Les composés d'amélioration de sapidité peuvent être combinés avec du café à un stade quelconque de son traitement pour augmenter la note de la tasse d'une boisson au café. Dans certains modes de réalisation, les composés d'amélioration de sapidité comprennent un ou plusieurs composés d'ester caféique, par exemple de l'acide caféique estérifié avec un cyclitol ou composé connexe.
PCT/US2019/051780 2018-09-18 2019-09-18 Nouvelles petites molécules qui améliorent les qualités de sapidité du café et de boissons associées Ceased WO2020061223A1 (fr)

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US17/277,465 US11856975B2 (en) 2018-09-18 2019-09-18 Method of enhancing flavor qualities of coffee
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EP3952667A1 (fr) 2019-04-06 2022-02-16 Cargill, Incorporated Modificateurs sensoriels
CA3135584A1 (fr) 2019-04-06 2020-10-15 Cargill, Incorporated Procedes de preparation d'une composition d'extrait botanique
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